US1494127A - Ebnst pbeiswebk - Google Patents
Ebnst pbeiswebk Download PDFInfo
- Publication number
- US1494127A US1494127A US1494127DA US1494127A US 1494127 A US1494127 A US 1494127A US 1494127D A US1494127D A US 1494127DA US 1494127 A US1494127 A US 1494127A
- Authority
- US
- United States
- Prior art keywords
- compound
- pbeiswebk
- ebnst
- acid
- new compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 description 28
- UORJNBVJVRLXMQ-UHFFFAOYSA-N Aprobarbital Chemical compound C=CCC1(C(C)C)C(=O)NC(=O)NC1=O UORJNBVJVRLXMQ-UHFFFAOYSA-N 0.000 description 12
- 229960003153 aprobarbital Drugs 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- -1 hydroxyl ions Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 2
- 230000000202 analgesic Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 230000001771 impaired Effects 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
Definitions
- My invention relates to a compound of isopropylallylbarbituric acid and process for making same, which consists in melting down isopropylallylbarbituric acid with I 1-phenyl-2, 3-dimethyl-4cdimethylamino-5- pyrazolone.
- dimethyl-4-dimethylainino-5'- pyrazolone is valuable, because it has been found that for producing sleep smaller doses are needed than correspond with its content of isopropylallylba'rbituric acid. It is of particular importance that the analgesic action of the new compound is a great deal stronger than that of the pure pyrazolone derivative; thus with the new compound it .is generally possible to produce sleep even vin-cases Where it is impaired by physical pain.
- the new compound may there ore partly replace the opiates.
- the new compound may obtained by melting down the two components in v.molecular proportions; when an excess of one or.
- the other of the components is used the prodnot is not homogenous, but consists of a mixture of the new compound with the component' of which an excess has been used, and the melting point is accordingly different from that of the pure compound. Even when one of the components is used in excess the mixture is stable. Simple mixtures of the two components, especially in tablet form, discolor gradually owing to the formation of the new compound at the points of contact.
Description
Patented May 13, 1924.
urrno STATES PATENT OFFICE.
ERNST PREISWERK. QF BASLE, SWITZERLAND, ASSIGNOR TO THE HOFFMBNfi- LA ROCHE CHEMICAL WORKS, OF NEW YORK, N. Y., A CORPORATION 035 NEW YORK.
(30111126173113 0'! ISQPROPYL'ALLYL BARBITURIC ACID AND PROCESS FOR HAKINGSAHE.
No Drawing. Application fileg. November 15, 1921, Serial No. 515,333. Renewed October 23, 1923.
To all whom it may concern.
Be it known that I, ERNST Pamswnnn, a citizen of Switzerland, and a resident of Basle, Switzerland, have invented certain new and useful Improvements in a Compound of Isopropyl Allyl Barbituric Acid and Process for Making Same, of which the following isa specification.
My invention relates to a compound of isopropylallylbarbituric acid and process for making same, which consists in melting down isopropylallylbarbituric acid with I 1-phenyl-2, 3-dimethyl-4cdimethylamino-5- pyrazolone. I
It has beerrfound that isopropylallylbarbituric acid and 1-phenyl-2, 3-dimethyl-4- dimethylamino-fi-pyrazolone form a new compound of peculiar properties. When melted down together the two colorless starting materials yield a yellow product whose melting point lies exactly between 92 and 93 C., provided that molecular parts have been used for the melting down. The reaction of the new compound towards solvents is varied. It is but slightly split up by carbohydrates; the solution obtained is of a deep yellow color. Solvents containing hydroxyl ions, especially water, yield slightly yellow so tions, which shows that in these solvents the compound is split up to a great extent. From such solutions it is possible to crystallize one of the two components without any admixture from the other. The new compound of isopropylallylbarbituric acid and 1-phenyl-2, 3-
dimethyl-4-dimethylainino-5'- pyrazolone is valuable, because it has been found that for producing sleep smaller doses are needed than correspond with its content of isopropylallylba'rbituric acid. It is of particular importance that the analgesic action of the new compound is a great deal stronger than that of the pure pyrazolone derivative; thus with the new compound it .is generally possible to produce sleep even vin-cases Where it is impaired by physical pain. The new compound may there ore partly replace the opiates.
The new compound may obtained by melting down the two components in v.molecular proportions; when an excess of one or.
the other of the components is used the prodnot is not homogenous, but consists of a mixture of the new compound with the component' of which an excess has been used, and the melting point is accordingly different from that of the pure compound. Even when one of the components is used in excess the mixture is stable. Simple mixtures of the two components, especially in tablet form, discolor gradually owing to the formation of the new compound at the points of contact.
E mam'ple.
10 parts of isopropylallylbarbituric acid I and 11 parts of l-phenyl-2, 3-dimethyl-4- dimethylamino 5-pyrazolone are mixed and heated to IUD-120. A clear yellow molten mass is obtained which, while stirring, is left to cool. The solid compound is then powdered. The powder is distinctly yellow,
its melting point lies-exactly between 92 and powder is absolutely stable.
ing, with solvents containing hydroxyl ions,
especially water, slightly yellow solutions.
In witness whereof I have hereunto set my hand.
ERNST PREISWERK.
Witnesses ALBERT A. HOFFMANN, HENRY KUBLI.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1494127A true US1494127A (en) | 1924-05-13 |
Family
ID=3406666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US1494127D Expired - Lifetime US1494127A (en) | Ebnst pbeiswebk |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1494127A (en) |
-
0
- US US1494127D patent/US1494127A/en not_active Expired - Lifetime
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